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Séminaire Chimie ED459

Foldamers : expanding the chemical space

Dr. Ivan Huc, D.R. CNRS (Institut Européen de Chimie Biologie, CNRS / Université de Bordeaux)

publié le , mis à jour le

Le Jeudi 17 Mars 2011 à 13h45
UM2, Salle de cours SC-16.01

Keywords : Synthetic oligomers, folding, structure analysis, biological function.

Our group has developed helical foldamers – oligomers that adopt stable helical folded conformations – derived from aromatic amino acids [1]. Some of these folded objects have shown unprecedented conformational stability [2], and constitute convenient building blocks to elaborate synthetic, very large (protein-sized) folded architectures (Figure 1) [3]. They possess a high propensity to assemble into double, triple and quadruple helices [4]. Cavities can be designed within such synthetic molecules that enable them to act as artificial receptors [5] including for chiral guests. Water soluble analogues of these foldamers show promise in nucleic acid recognition [6].

Figure 1 (cliquer pour l’agrandir)

Figure 1. Crystal structure of a large foldamer comprised of two helices of opposite handedness at a 90° angle. The protein crystal structure on the right is shown as the same scale for size comparison.

References

1. S. Hecht, I. Huc (Eds), Foldamers : Structure, Properties, and Applications, 2007, Wiley-VCH, Weinheim, ISBN : 978-3-527-31563-5.
2. H. Jiang, J.-M. Léger, I. Huc, J. Am. Chem. Soc. 2003, 125, 3448 ; N. Delsuc, T. Kawanami, J. Lefeuvre, A. Shundo, H. Ihara, M. Takafuji, I. Huc ChemPhysChem 2008, 9, 1882.
3. C. Dolain, J.-M. Léger, N. Delsuc, H. Gornitzka, I. Huc Proc. Natl. Acad. Sci. USA 2005, 102, 16146 ; N. Delsuc, J.-M. Léger, S. Massip, I. Huc Angew. Chem. Int. Ed. 2007, 46, 214 ; D. Sánchez-García, B. Kauffmann, T. Kawanami, H. Ihara, M. Takafuji, M.-H. Delville, I. Huc, J. Am. Chem. Soc. 2009, 131, 8642.
4. Q. Gan, C. Bao, B. Kauffmann, A. Grélard, J. Xiang, S. Liu, I. Huc, H. Jiang, Angew. Chem. Int. Ed. 2008, 47, 1715 ; D. Haldar, H. Jiang, J.-M. Léger, I. Huc, Angew. Chem. Int. Ed. 2006, 45, 5483 ; Y. Ferrand, A. Kendhale, J. Garric, B. Kauffmann, I. Huc, Angew. Chem. Int. Ed. 2010, 49, 1718.
5. Bao, B. Kauffmann, Q. Gan, K. Srinivas, H. Jiang ; I. Huc Angew. Chem. Int. Ed. 2008, 47, 4153 ; Y. Ferrand, A. M. Kendhale, B. Kauffmann, A. Grélard, C. Marie, V. Blot, M. Pipelier, D. Dubreuil, I. Huc, J. Am. Chem. Soc. 2010, 132, 7858.
6. P. S. Shirude, E. R. Gillies, S. Ladame, F. Godde, K. Shin-ya, I. Huc, S. Balasubramanian, J. Am. Chem. Soc. 2007, 129, 11890.

Contact IBMM (DAPP) : Isabelle Parrot

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